Celebrities You Didn’t Realize Went to School Together

We’re just going to dive right in with one of the biggest head scratchers there is. Yep, it’s true, the girl from Something About Mary and one of the most legendary gangster rappers of all-time actually went to high school together. That’s not to say they were paling around or anything, but they definitely did interact, at least according to Diaz. They both went to Long Beach Polytechnic, and they met in the most obvious way imaginable when you’re talking about Snoop Dogg: she bought weed from him. Snoop was a year older, which is why he said he never tried to hit on her despite her being a hot cheerleader.

It’s really not hard to fathom that a couple of guys like BJ Novak and John Krasinski could have gone to school together, until you take into account they both got their big break in Hollywood on the exact same show. The pair both starred – and in the case of Novak, wrote – The Office, which is kind of an amazing coincidence considering they actually went to high school together in Massachusetts. Not only that, but Novak claims responsibility for Krasinski’s acting career. See, it turns out that Novak cast Krasinski in a role in a play that Novak wrote and directed their senior year, and the rest, as they say, is history.

How does someone go from one of the most influential, hardcore rappers of all-time, to the Fresh Prince? Well, you’d have to ask Jada Pinkett-Smith, who grew up with Tupac and not only went to high school with the late, great rapper, but actually dated him when they were in their teens. It must have been a little bit of a weird relationship, of course, considering the fact that Pinkett-Smith has described Tupac as a “father figure” in interviews which is…a little creepy. Anyway, obviously later in life she gave up the gangster rappers and moved on to the more family friendly purveyor of rhymes in Will Smith.

Maybe the really surprising thing about learning that not only are Val Kilmer and Kevin Spacey dear friends, but they’re actually the same age. The once seemingly perpetually young Kilmer – who, admittedly, is no longer baby faced and pretty like he used to be – and Spacey, whose career took off later in life went to high school together in California. According to Kilmer, it was actually Spacey who was a lousy actor in high school, though. Of course that didn’t stop their drama teacher from casting Spacey as one of the leads in their production of Sound of Music, which co-starred another future famous actress in Mare Winningham.

We don’t even have to stop at those four famous actors, by the way, since Charlie’s brother Emilio Estevez also went to school with Penn, Downey, and Lowe. It’s hard to fathom a more star studded graduating class than this group that attended Santa Monica High. According to Lowe, Charlie Sheen would actually wear bulletproof vests to school because he was utterly convinced gang members were gunning for him. Despite Sheen clearly being fairly insane even back then, the group was tightly knit through high school, and would obviously go on to be some of the most famous names in Hollywood. Well, aside from Emilio, anyway. When your most memorable role is as a pee-wee hockey coach, you can’t really claim a whole lot of fame.

Anderson Cooper is one of those guys whose age has always been hard to peg because the dude has just seemingly always had white hair. You know, kind of like Steve Martin. However, if you want to get a general idea of how old the CNN host actually is, here’s a hint: he went to high school with Christian Slater, better known as the former teen heart-throb who so desperately wanted to be the next Jack Nicholson. The pair both attended the Dalton School in New York, which is about as ritzy as you probably guessed based on that name. After all, an important thing to remember about Cooper and where he comes from: he’s a freaking Vanderbilt. So, yeah, he comes from a little bit of money.

Lauryn Hill has kind of dropped off the map these days, in part because she seemingly went a little crazy, but there was a time when she was the absolute biggest female star in the entire music industry. And as it turns out, she went to high school and was good friends with Zach Braff, the nerdy, goofy star of Scrubs and Garden State. Hill kind of made a name for herself as being kind of militant about her heritage, but according to an interview Braff did with Howard Stern, she was nothing like that when they were growing up. Obviously, people and their views can change, but from Braff’s description it sounds like she was more like one of the Cosby kids than the hardcore rapper and singer she would grow into.

If you were walking around the halls of DeWitt Clinton High School in New York in the late 1930’s, you’d stand a solid chance of bumping into one of the most famous boxers of all-time, and then a moment later, the most legendary comic book writer in history. “Sugar” Ray Robinson and Stan “The Man” Lee both went to DeWitt, and while we have absolutely no reason to believe they were actually pals, isn’t it nice to imagine that the original Sugar Ray was besties with the guy who created Spider-Man? Oh, and another fun note about DeWitt: not only the creator of Spider-Man and, well, pretty much the entire roster of Marvel heroes graduate, but so did Bob Kane and Bill Finger. Or, if those names don’t mean anything to you, the two guys who created freaking Batman.